You may be surprised to learn that not every politician is equipped with romantic game. Here are the stories of a few presidents who had a little difficulty garnering the affections of the first lady – or at least had a few awkward moments during the courtship. Learn from their fumbles, and be grateful that your own aren’t subject to public scrutiny.

1. John Adams’ Ill-Timed Inoculation

If you’re seriously pursuing a woman, try not to get quarantined midway through courtship. That’s exactly what happened to John Adams soon after he began dating Abigail. Because Adams spent a significant amount of time in Boston, where the smallpox epidemic was raging, he opted to get vaccinated. The procedure required a six-week quarantine, during which all physical contact was forbidden.

While Abigail was delighted to receive notes from her sweetheart during his time away, she was so fearful of catching smallpox that she requested that John thoroughly “smoke” the letters before sending them. She wrote, “I hope you smoke your letters well, before you deliver them. Mamma is so fearful lest I should catch the distemper, that she hardly ever thinks the letters are sufficiently purified.” Upon their arrival, Abigail would ask her slave to smoke them one more time and hovered over him while he did. Though the notes themselves were quite heartfelt, the smoky smell definitely made them a tad less romantic.

2. Woodrow Wilson and the Embarrassing Typo

Woodrow Wilson didn’t actually have a problem enticing his wife-to-be Edith Galt to go out with him; the awkwardness came after they’d already been dating. The two began seeing each other in 1915, a year after Wilson’s first wife, Ellen, had passed away. Fearing that critics would condemn him for moving on too quickly, 59-year-old Wilson kept the relationship on the down-low. But one day, the Washington Post published a news blurb exposing the couple’s night out on the town. The article was supposed to read, “Rather than pay attention to the play, the president spent the evening entertaining Mrs. Galt.” But an unfortunate typo stated, “... the president spent the evening entering Mrs. Galt.”

3. Richard Nixon’s Strange Chauffeur Service

Nixon was never exactly a ladies man. When he proposed to his future wife Pat on their first date, she thought he was nuts. But that didn’t deter him. Instead, Nixon offered to be her driver on her dates with other men. He also inundated her with mushy love letters, referring to himself in the third person and to Pat as “thee.” One line read, “When the wind blows and the rains fall and the sun shines through the clouds (as it is now) he still resolves. . . that nothing so fine ever happened to him or anyone else as falling in love with Thee -- my dearest heart.”

Pat’s replies were a little more succinct. She wrote back, “In case I don't see you before, why don't you come early Wednesday and I'll see if I can burn a hamburger for you." But despite her apparent lack of interest, Pat eventually came around and let Nixon drive her on more dates - this time with himself.

4. Calvin Coolidge’s Lasting First Impression

Grace Donahue Goodhue first spotted the demure Calvin Coolidge through a boarding house window while she was watering flowers outside. At that moment, he happened to be shaving in front of a mirror wearing nothing but long underwear and a derby hat - which he claimed was to keep the hair out of his eyes. Grace burst out laughing, causing Coolidge to turn and see her glancing up at him from the street below. Not only did the long johns and shaving cream not catch on – the notoriously reserved president also had to endure decades of taunting from his wife... and everyone else who heard the tale of their initial encounter.

5. Harry Truman’s Unrelenting Love Letters

Truman was acutely aware of his lack of romantic game, admitting, “I was always afraid of girls my age and older.” But when he met Bess Wallace at Sunday school, it was love at first sight. However, while he only had eyes for her, it took almost 30 years before she reciprocated his passion. As adults, Truman began inundating her with over-the-top love letters. In one 1911 note, he opened with remarks about the weather, seamlessly transitioning into a marriage proposal. “Water and potatoes will soon be as much of a luxury as pineapples and diamonds," he wrote. "Speaking of diamonds, would you wear a solitaire one on your left hand should I get it?”

Bess said no. But Truman kept at it, proclaiming his unwavering dedication. In one letter, he declared that if she ever accepted his offer – “I'd make love to you so hard you'd either have to say yes or knock me on the head” – but then promptly apologized for his forwardness. But perhaps that kind of talk was convincing. In 1913, two and a half years after Truman’s original proposal, Bess said her feelings had changed. In 1919, the two finally tied the knot, and Harry moved in with Bess and her mother. Yup, Truman was a smooth operator right up until the very end.

6. Grover Cleveland Robs the Cradle

The only president to serve two non-consecutive terms was also the only president married in a White House ceremony. Grover Cleveland was 49 and a little more than a year into his first term when he married 21-year-old Frances Folsom. Cleveland had known his bride her whole life. Her father was a close friend of the future president, and Cleveland bought the infant Frances a baby carriage as a gift. Growing up she called him "Uncle Cleve." When her father died leaving no will, the court appointed Cleveland to administer the estate.

The wedding was a simple affair, attended by close friends, family, and cabinet members and their wives. But the occasion was far from quiet—John Philip Sousa led the Marine Band. After the ceremony, "the ladies kissed the bride to their hearts content," The New York Times reported, "but the gentlemen followed the example of the groom and refrained." There was a 20-pound salmon to sup on and a 25-pound wedding cake.

7. Barack Obama’s Workplace Romance

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When Michelle Robinson was assigned to be Barack Obama’s supervisor while he worked as a summer associate at a Chicago law firm, she took one look at his file and said, “This guy’s gotta be kind of weird.” For some reason, Michelle thought his exotic name and prestigious pedigree (Harvard Law School, which she also attended) screamed “Steve Urkel” louder than “marriage material.” After meeting Barack, she admitted that he was cuter than she’d expected, but resolved to keep the relationship strictly professional, even after he asked her out multiple times. Finally, after a good bit of nagging on his part, she eventually acquiesced and agreed to hang out—as long as they didn’t call it a date. But after a day filled with art museums, jazz clubs, and Spike Lee, Michelle decided to give the whole romance in the workplace thing a try. In Barack’s case, persistence paid off.

Note: The Grover Cleveland section was written by David Holzel for a previous article on White House Weddings.